Jimmy Kimmel's Real-Life BFF Is Almost As Controversial As Trump

Remember that radio show Donald Trump used to frequent? The one where he spoke approvingly about his eldest daughter, Ivanka Trump's body, his questionable sexual encounters with women, and gave the host permission to call Ivanka a "piece of a**"? (via CNN). That was "The Howard Stern Show," and while its shock jock host has made a U-turn when it comes to his level of controversy over the years, Stern is still most remembered for his glory days and known to be good friends with late-night talk show host Jimmy Kimmel, who has had his own controversial moments we can't forget about (albeit far less). During Stern's 2019 appearance on "Jimmy Kimmel Live!" the duo's close relationship was on full display, with the iconic radio host gushing, "I wanted to tell you how much I love you," to which Kimmel happily responded, "I love you too." 

Stern then proceeded to serenade his buddy with a song. It's rather ironic that the late-night host is friends with someone who is almost as divisive as Trump since Kimmel is known for being highly critical of him. Stern's list of controversies is as long as the president's list of felonies, and some of his past comments have come back to bite him. In 2024, as the radio host was readying to interview Former Vice President Kamala Harris, a 1993 clip of him appearing in blackface and using racial slurs made the rounds. It wasn't a good look, nor was a resurfaced video of him commenting on actress Sofía Vergara's breasts, which circulated on social media in August 2025. At one point during the 2003 interview, Stern told Vergara, "If you don't want to go out with me, then at least let me feed from your chest," (via X, formerly known as Twitter).

Jimmy Kimmel's late night show suspension in September 2025 had everyone laying into Donald Trump, for encouraging it so strongly, including Howard Stern, who revealed on "The Howard Stern Show" that he had called his pal to ask how he was holding up. The famously outspoken shock jock condemned ABC's decision to bow to pressure from the White House to take Kimmel off the air, proclaiming simply, "I just know when the government begins to interfere, when the government says, 'I'm not pleased with you, so we're gonna orchestrate a way to silence you,' it's the wrong direction for our country, and I should know," (via Instagram).

Indeed, given that controversy was the foundation on which Stern's show was built in its heyday, it comes as no surprise that he's had his fair share of run-ins with the Federal Communications Commission (FCC). ABC ultimately decided to backtrack on its decision to take "Jimmy Kimmel Live!" off the air, and Kimmel wasted no time torpedoing Donald Trump's ego upon his return. Stern joked that he was the one to thank for the company's change of heart because he promised his audience he was going to cancel his Disney+ subscription, quipping, "See, problem solved, all I had to do was mention I was canceling my subscription," (via Facebook).